Hydrochloric Acid → 2-(1-Naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid

HRID 1606607Notes

Reaction equation

HRID 1606607 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C([N:18]([CH2:21][CH3:22])CC)C.COCCO[CH2:28][CH2:29]OC.Cl>O>[C:22]1([CH2:21][NH:18][C:2]2[CH:10]=[C:9]([Cl:11])[C:8]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[C:28]2[C:29](=[CH:10][CH:2]=[CH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8150DiglymeHCID 8471TriethylamineHCID 2210136551521-75-6

Product 1

HCID 215439942-(1-Naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-Dichloro-5-methylsulfonylbenzoic acid (5.4 g.; 0.02 mole), 1-aminomethylnaphthylene (3.2 g.; 0.02 mole), and triethylamine (4 ml.) are added to diglyme (50 ml.). The resulting solution is refluxed with stirring for 4 hours. The reaction solution is cooled to room temperature and is slowly added to a solution of concentrated hydrochloric acid (10 ml.) in water (150 ml.) The aqueous layer is decanted from the viscous oil that separates. This viscous oil is dissolved in ethanol (25 ml.) and the resulting solution is poured into water. The tan colored solid which precipitates is collected and dried, yield 5.5 g. (70%). After several recrystallizations from acetonitrile, the 2-(1-naphthylmethyl)amino-4-chloro-5-methylsulfonylbenzoic acid melts at 242°-246° C. (dec. with eff.).

Workup

  1. temperatureThe resulting solution is refluxed
  2. customis decanted from the viscous oil that separates
  3. dissolutionThis viscous oil is dissolved in ethanol (25 ml.)
  4. additionthe resulting solution is poured into water
  5. customThe tan colored solid which precipitates
  6. customis collected
  7. customdried
  8. customAfter several recrystallizations from acetonitrile

Sources & evidence

ORD record
ord-09d3f72c4529462690ad95685f89b234
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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